Organic Chemistry at Yale

Published on: 08/17/11

Zef Konst ’12, a chemistry major, enjoyed volunteering in the lab of Yale Assistant Professor of Chemistry Seth Herzon last summer so much that he decided to do it again. This time he is working at Professor Herzon’s lab with the support of the Koshland Integrated Natural Science Center and hopes to use his experiences this summer as a foundation for his senior thesis research. Konst will be taking his fall semester off from Haverford to conduct his thesis research with Professor Herzon at Yale.

Professor Herzon’s lab studies the synthesis of natural products and the development of synthetic methods. Konst’s research is focused on the spiroquinazoline molecule. Spiroquinazoline, a fungal metabolite, was discovered and first described in a 1994 article in the Journal of Natural Products. It is a member of the alkaloid family, whose member molecules contain nitrogen and many are produced by plants. Common alkaloids include cocaine, nicotine, caffeine, and morphine. Molecules can by created in the lab with the same composition found in nature, but the elements aren’t always organized with the same geometry, says Konst. The structure can sometimes adopt mirror image configurations, with the same overall atomic content, but different properties.

Konst is trying to create a spiroquinazoline molecule that is enantiomerically pure, or an exact geometrical replica of the natural molecule. He is using a process called retrosynthesis, in which scientists look at fully formed molecules and mentally deconstruct them, working backwards to figure out the pieces of the puzzle. Konst says that there are currently no known therapeutic uses for spiroquinazoline, but he is enjoying the opportunity to conduct research on the molecule to better understand its potential. “Organic synthesis has developed to such a sophisticated level that the focus is no longer on whether a molecule can be made or not, but if it can be made efficiently and in an enantiomerically pure form,” he says.

Working for Professor Herzon has been a motivational experience for Konst, who hopes to one day receive a Ph.D. in Chemistry and enter either academia or the pharmaceutical industry. Konst remembers one of his early experiences this summer: “I came up with a 15-step stereoselective route with lots of help from the post docs and graduate students in the lab that I thought was alright. When I showed it to my professor, he took it home for the night and came back the next morning with an amazing retrosynthesis of my molecule that was both stereoselective and efficient. This was the most inspirational part of my summer because he showed such a comprehensive knowledge of organic chemistry as well as creativity that I think every organic chemist strives for.”

Konst is also a member of the Haverford College men’s varsity squash team, which he has co-captained the last two years. While at Yale, he has continued to play with co-workers and graduate students.